Cycloreversion of azetidines via oxidative electron transfer. steady-state and time-resolved studies.
Cycloreversion of cis- and trans-1,2,3-triphenylazetidine (c-2 and t-2) is achieved by electron transfer to (tris(4-bromophenyl)aminium radical cation (5 (*+)). Stepwise C-N and C-C bond cleavage of azetidine radical cations leads to cis- and trans-stilbene, together with N-benzylideneaniline, as final products. Mechanistic evidence is provided by quenching studies, using laser flash photolysis to generate 5 (*+) from its neutral precursor.
Andreu
Inmaculada
I
Departamento de Química/Instituto de Tecnología Química UPV-CSIC, Universidad Politécnica de Valencia, Valencia, Spain.
Delgado
Julio
J
Espinós
Amparo
A
Pérez-Ruiz
Raul
R
Jiménez
M Consuelo
MC
Miranda
Miguel A
MA
D001384:Azetidines / Q000737:chemistry*; D003500:Cyclization; D004579:Electron Transport; D009942:Organometallic Compounds / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013997:Time Factors
D001384:Azetidines; D009942:Organometallic Compounds; D000644:Quaternary Ammonium Compounds; C079938:tris(4-bromophenyl)ammoniumyl hexachloroantimonate; C082735:azetidine